(E)-1-(4-Decyl­oxyphen­yl)-3-(4-hydroxy­phen­yl)prop-2-en-1-one

Ibrahim Abdul Razak; Hoong-Kun Fun; Zainab Ngaini; Siti Muhaini Haris Fadzillah; Hasnain Hussain

doi:10.1107/S160053680901054X

. 2009 Mar 28;65(Pt 4):o881–o882. doi: 10.1107/S160053680901054X

(E)-1-(4-Decyloxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Ibrahim Abdul Razak ^a,^*, Hoong-Kun Fun ^a,^‡, Zainab Ngaini ^b, Siti Muhaini Haris Fadzillah ^b, Hasnain Hussain ^c

PMCID: PMC2969075 PMID: 21582591

Abstract

In the title compound, C₂₅H₃₂O₃, the asymmetric unit contains two crystallographically independent molecules: both enone groups adopt an s-cis configuration. In the crystal, O—H⋯O and C—H⋯O intermolecular interactions form bifurcated hydrogen bonds, which generate R ¹ ₂(6) ring motifs. These intermolecular interactions link the molecules into one-dimensional chains along the [10 Inline graphic ] direction. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For general background to the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Satyanarayana et al. (2004 ▶); Zhao et al. (2005 ▶); Yayli et al. (2006 ▶). For related structures, see: Ng, Razak et al. (2006 ▶); Ng, Patil et al. (2006 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₅H₃₂O₃
M _r = 380.51
Monoclinic,
a = 12.4437 (2) Å
b = 35.5191 (6) Å
c = 9.8004 (2) Å
β = 99.284 (1)°
V = 4274.93 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.52 × 0.44 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.962, T _max = 0.974
62626 measured reflections
16928 independent reflections
12634 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.153
S = 1.04
16928 reflections
515 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901054X/at2746sup1.cif

e-65-0o881-sup1.cif^{(36.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901054X/at2746Isup2.hkl

e-65-0o881-Isup2.hkl^{(827.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯O2Bⁱ	0.91 (2)	1.80 (2)	2.711 (1)	179 (3)
O1B—H1OB⋯O2Aⁱⁱ	0.91 (2)	1.81 (2)	2.716 (1)	176 (2)
C4A—H4AA⋯O2Bⁱ	0.93	2.50	3.185 (1)	131
C4B—H4BA⋯O2Aⁱⁱ	0.93	2.50	3.192 (1)	131
C14B—H14B⋯O3A	0.93	2.56	3.485 (1)	173
C18B—H18C⋯Cg1ⁱⁱⁱ	0.97	2.85	3.696 (1)	146
C24B—H24D⋯Cg2ⁱⁱⁱ	0.97	2.71	3.554 (1)	145
C22A—H22B⋯Cg3^iv	0.97	2.95	3.743 (1)	140

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C10B–C15B and C1B–C6B rings, respectively.

Acknowledgments

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312 and the Research University Golden Goose grant No.1001/PFIZIK/811012. ZN and HH thank Universiti Malaysia Sarawak for the Geran Penyelidikan Dana Khas Inovasi, grant No. DI/01/2007(01). SMHF thanks the Malaysian Government and Universiti Malaysia Sarawak for a providing scholarship for postgraduate studies.

supplementary crystallographic information

Comment

Chalcone derivatives are reported to possess biological properties such as anticancer (Bhat et al., 2005), antimalarial (Xue et al., 2004), antioxidant and antimicrobial activities (Yayli et al., 2006), antiplatelet activity (Zhao et al., 2005) as well as antihyperglycemic activity (Satyanarayana et al., 2004). Chalcone derivatives possessing alkyl chains have been synthesized in our lab and their antibacterial activities were tested against E. coli ATCC 8739. All the synthesized chalcone derivatives showed antimicrobial activity. The structure reported in this paper, (I), is one of the chalcone derivatives mentioned above.

There are two crystallographically independent molecules (A and B) in the asymmetric unit (Fig. 1). The bond lengths observed in (I) show normal values as reported by Allen et al., 1987. These two molecules (A and B) are interconnected by C14B—H14B···O3A intermolecular interactions (Table 1). In molecule A, the mean plane through the enone moiety (O2C7C8C9) and the two benzene rings make dihedral angles of 0.59 (7)° (C1—C6) and 4.49 (6)° (C10—C15) whereas in B, these angles are 4.21 (7)° (C1—C6) and 8.66 (7)° (C10—C15). The dihedral angles between the two benzene rings are 5.08 (5)° for molecule A and 9.23 (5)° for B. The alkoxyl tail in both molecules is coplanar with the attached ring with the torsion angle (C16—O3—C13—C12) in molecule B [5.06 (15)°] larger than in A [1.79 (15)°].

The enone moieties of both molecules adopt s-cis configuration with C7—C8—C9—O2 torsion angle being -1.2 (2)° for molecule A and -7.3 (2)° for B. The widening of C1A—C6A—C7A (123.94 (9)°) and C6A—C7A—C8A (128.28 (9)°) angles in molecule A is the result of the short H1AA···H8AA(2.32 Å) contact whereas short H8AA···H15A (2.17 Å) contact widened the C9A—C10A—C15A (124.53 (9)°). Similarly in molecule B, close interatomic contact between H1BA and H8BA (2.35 Å) results in the widening of C1B—C6B—C7B (124.33 (9)°) and C6B—C7B—C8B (129.01 (10)°) angles whereas the opening of C9B—C10B—C15B angle to 124.13 (9)° is the result of the close H8BA···H15B (2.18 Å) contact. Similar feature was also discussed in structures reported by Ng, Razak et al. (2006) and Ng, Patil et al. (2006).

In the crystal structure, O1A—H1OA···O2Bⁱ and C4A—H4AA···O2Bⁱ interactions in molecule A and O1B—H1OB···O2Aⁱⁱ and C4B—H4BA···O2Aⁱⁱ in B (Table 1) form bifurcated acceptor bonds which generate R¹₂(6) ring motifs (Fig. 2). These intermolecular interactions translate the molecules into one-dimensional extended chains along the [1 0 -1] direction. The crystal structure is further stabilized by C—H···π interactions (Table 1).

Experimental

A mixture of 4-hydroxybenzaldehyde (2.44 g, 20 mmol) and 4-decyloxyacethophenone (5.53 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in 60 ml of methanol was heated at reflux for 24 h. The reaction was cooled to room temperature and was acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. The precipitate was dissolved in hexane–ethanol (7:1) mixture. After a few days of slow evaporation, crystals suitable for X-ray analysis were collected.